Hypatulone A, a Homoadamantane-Type Acylphloroglucinol
with an Intricately Caged Core from Hypericum patulum
Posted on 2018-12-10 - 11:29
Hypatulone
A (1), an acylphloroglucinol possessing an unprecedented
homoadamantane architecture based on a tricyclo-[4.3.1.13,8]-undecane core and a unique 5/5/7/6/6 pentacyclic ring system, together
with its biogenetic precursor hyperbeanol B (2), was
isolated from Hypericum patulum. The
structure of 1 was elucidated by extensive spectroscopic
analysis and electronic circular dichroism calculation. Its plausible
biosynthetic pathway via Wagner–Meerwein rearrangement was
proposed. 1 exhibited nitric oxide inhibitory effect
on LPS-induced RAW264.7 cell line (IC50 18.8 ± 1.75
μM).
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Liu, Yang-Yang; Ao, Zhen; Xue, Gui-Min; Wang, Xiao-Bing; Luo, Jian-Guang; Kong, Ling-Yi (2018). Hypatulone A, a Homoadamantane-Type Acylphloroglucinol
with an Intricately Caged Core from Hypericum patulum. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b03523
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AUTHORS (6)
YL
Yang-Yang Liu
ZA
Zhen Ao
GX
Gui-Min Xue
XW
Xiao-Bing Wang
JL
Jian-Guang Luo
LK
Ling-Yi Kong
KEYWORDS
ICpentacyclicHypericum patulum Hypatulone18.8coreIntricately Caged CoreHomoadamantane-Type Acylphloroglucinolhomoadamantane architecturerearrangementacylphloroglucinolspectroscopic analysisbiosynthetic pathway1.75nitric oxideundecanebiogenetic precursor hyperbeanol BWagnertricycloHypericum patulumdichroism calculationLPS-induced RAW 264.7 cell line